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Synlett 2023; 34(11): 1215-1229
DOI: 10.1055/a-2010-7874
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The Untold Journey of Total Synthesis of Natural Products

Rongbiao Tong  ∗
a   Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, P. R. of China
b   The Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), Nansha, Guangzhou 511458, P. R. of China
› Author AffiliationsThis research was financially supported by the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) (SMSEGL20Sc01-B), and Research Grant Council of Hong Kong (C6026-19G, 16307219, 16306920, and 16300921).
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Abstract

This personal Account presents the developments of two synthetic strategies (Phenol Oxidative Dearomatization, POD; and Furan Oxidative dearomatization, FOD) for total synthesis of natural products. The POD program was originally derived from our first total synthesis of tenuipyrone, while our productive FOD program arose from the total synthesis of the uprolide family. Instead of a review summary of our total synthesis, this Account is focused on how these total synthesis projects are conceived and connected from the perspective of laboratory development. It is evident that total synthesis is not an isolated event, but a connecting and inspirational point that sparks new ideas and new projects.

1 Introduction

2 Total Synthesis versus Synthetic Methodology

3 Development of Phenol Oxidative Dearomatization (POD) for Total Synthesis

4 Development of Furan Oxidative Dearomatization (FOD, Achmatowicz rearrangement) for Total Synthesis

5 Conclusion and Outlook

Key words

total synthesis - natural product - dearomatization - Achmatowicz rearrangement - o-quinone methide


Publication History

Received: 30 December 2022

Accepted: 11 January 2023

Accepted Manuscript online:
11 January 2023

Article published online:
15 February 2023

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  • References

  • 1 Hoffmann R. Angew. Chem., Int. Ed. Engl. 1988; 27: 1593
    Crossref
  • 2 Asai T, Chung Y.-M, Sakurai H, Ozeki T, Chang F.-R, Yamashita K, Oshima Y. Org. Lett. 2012; 14: 513
    CrossrefPubMed
  • 3 Song L, Yao H, Zhu L, Tong R. Org. Lett. 2013; 15: 6
    CrossrefPubMed
  • 4 Kusuda S, Ueno Y, Toru T. Bull. Chem. Soc. Jpn. 1993; 66: 2720
    Crossref
  • 5 Yao HL, Song LY, Liu Y, Tong R. J. Org. Chem. 2014; 79: 8774
    CrossrefPubMed
  • 6 Barradas S, Urbano A, Carreño MC. Chem. Eur. J. 2009; 15: 9286
    CrossrefPubMed
  • 7 Song LY, Liu Y, Tong R. Org. Lett. 2013; 15: 5850
    CrossrefPubMed
  • 8 Song LY, Lee KH, Lin ZY, Tong R. J. Org. Chem. 2014; 79: 1493
    CrossrefPubMed
  • 9 Ackland MJ, Hanson JR, Hitchcock PB, Ratcliffe AH. J. Chem. Soc., Perkin Trans. 1 1985; 843
    Crossref
  • 10 Wang J, Tong R. J. Org. Chem. 2016; 81: 4325
    CrossrefPubMed
  • 11 Wang J, Tong R. Org. Lett. 2016; 18: 1936
    CrossrefPubMed
  • 12 Wong Y.-S. Chem. Commun. 2002; 686
    CrossrefPubMed
  • 13 Song LY, Yao HL, Dai YJ, Wu MW, Tong RB. Tetrahedron Lett. 2016; 57: 4257
    Crossref
  • 14 Yao HL, Song LY, Tong R. J. Org. Chem. 2014; 79: 1498
    CrossrefPubMed
  • 15 Song LY, Yao HL, Tong R. Org. Lett. 2014; 16: 3740
    CrossrefPubMed
  • 16 Wei L, Xiao M, Xie Z. Org. Lett. 2014; 16: 2784
    CrossrefPubMed
  • 17 Song L, Huang F, Guo L, Ouyang M.-A, Tong R. Chem. Commun. 2017; 53: 6021
    CrossrefPubMed
  • 18 Song L, Su Q, Lin X, Du Z, Xu H, Ouyang M.-A, Yao H, Tong R. Org. Lett. 2020; 22: 3004
    CrossrefPubMed
  • 19 Rodríguez AD, Soto JJ, Barnes CL. J. Org. Chem. 2000; 65: 7700
    CrossrefPubMed
  • 20 Zhu L, Liu Y, Ma R, Tong R. Angew. Chem. Int. Ed. 2015; 54: 627
    CrossrefPubMed
  • 21 Zhu LY, Tong R. Synlett 2015; 26: 1643
    Article in Thieme Connect
  • 22 Zhu LY, Tong R. Org. Lett. 2015; 17: 1966
    CrossrefPubMed
  • 23 Liang LX, Guo LD, Tong R. Acc. Chem. Res. 2022; 55: 2326
    CrossrefPubMed
  • 24 Zhu LY, Song LY, Tong R. Org. Lett. 2012; 14: 5892
    CrossrefPubMed
  • 25 Li ZL, Leung TF, Tong R. Chem. Commun. 2014; 50: 10990
    CrossrefPubMed
  • 26 Li ZL, Ip FC. F, Ip NY, Tong R. Chem. Eur. J. 2015; 21: 11152
    CrossrefPubMed
  • 27 Li ZL, Tong R. Synthesis 2016; 48: 1630
    Article in Thieme Connect
  • 28 Li ZL, Tong R. J. Org. Chem. 2017; 82: 1127
    CrossrefPubMed
    • 29a Zhao GD, Canterbury DP, Taylor AP, Cheng XY, Mikochik P, Bagley SW, Tong R. Org. Lett. 2020; 22: 458
      CrossrefPubMed
    • 29b Liaw MW, Cheng WF, Tong R. J. Org. Chem. 2020; 85: 6663
      CrossrefPubMed
  • 30 Li Z, Tong R. J. Org. Chem. 2016; 81: 4847
    CrossrefPubMed
  • 31 Marquez-Cadena MA, Ren JY, Ye WK, Qian PY, Tong RB. Org. Lett. 2019; 21: 9704
    CrossrefPubMed
  • 32 Nakamura Y, Kato H, Nishikawa T, Iwasaki N, Suwa Y, Rotinsulu H, Losung F, Maarisit W, Mangindaan RE. P, Morioka H, Yokosawa H, Tsukamoto S. Org. Lett. 2013; 15: 322
    CrossrefPubMed
  • 33 Zhang W, Tong R. J. Org. Chem. 2016; 81: 2203
    CrossrefPubMed
  • 34 Ren JY, Liu Y, Song LY, Tong R. Org. Lett. 2014; 16: 2986
    CrossrefPubMed
  • 35 Ren JY, Tong R. J. Org. Chem. 2014; 79: 6987
    CrossrefPubMed
  • 36 Ren JY, Wang J, Tong R. Org. Lett. 2015; 17: 744
    CrossrefPubMed
  • 37 Guo LD, Xu Z, Tong R. Angew. Chem. Int. Ed. 2022; 61: e202115384
    CrossrefPubMed
  • 38 Zhao GD, Liang LX, Wang EY, Tong R. ACS Catal. 2021; 11: 3740
    CrossrefPubMed
  • 39 Wang J, Marquez-Cadena MA, Tong R. Org. Lett. 2020; 22: 5074
    CrossrefPubMed
  • 40 Ma FQ, He CX, Wang EY, Tong R. Org. Lett. 2021; 23: 6583
    CrossrefPubMed
  • 41 Zhao GD, Liang LX, Wen CH. E, Tong R. Org. Lett. 2019; 21: 315
    CrossrefPubMed